CN114773168A - Method for synthesizing cis/trans-prenyl-3-methyl butadiene ether by using methyl butynol and isopentenol - Google Patents
Method for synthesizing cis/trans-prenyl-3-methyl butadiene ether by using methyl butynol and isopentenol Download PDFInfo
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- CN114773168A CN114773168A CN202210457180.0A CN202210457180A CN114773168A CN 114773168 A CN114773168 A CN 114773168A CN 202210457180 A CN202210457180 A CN 202210457180A CN 114773168 A CN114773168 A CN 114773168A
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 64
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims abstract description 40
- JQZGUQIEPRIDMR-UHFFFAOYSA-N 3-methylbut-1-yn-1-ol Chemical compound CC(C)C#CO JQZGUQIEPRIDMR-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 23
- QVDTXNVYSHVCGW-ONEGZZNKSA-N isopentenol Chemical compound CC(C)\C=C\O QVDTXNVYSHVCGW-ONEGZZNKSA-N 0.000 title claims abstract description 21
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 230000000996 additive effect Effects 0.000 claims abstract description 15
- 239000000654 additive Substances 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 238000004817 gas chromatography Methods 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 238000012544 monitoring process Methods 0.000 claims abstract description 3
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 claims abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 238000001914 filtration Methods 0.000 claims description 13
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 8
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 8
- 229940045803 cuprous chloride Drugs 0.000 claims description 8
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 229960003280 cupric chloride Drugs 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001868 cobalt Chemical class 0.000 claims description 2
- 150000002505 iron Chemical class 0.000 claims description 2
- 150000002696 manganese Chemical class 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007524 organic acids Chemical group 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 claims 7
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 abstract description 25
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 abstract description 22
- 229940043350 citral Drugs 0.000 abstract description 19
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- -1 aldehyde monoterpene Chemical class 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OHCMANJUZNNOQW-UHFFFAOYSA-N 2,4,4-trimethylcyclohexene-1-carbaldehyde Chemical compound CC1=C(C=O)CCC(C)(C)C1 OHCMANJUZNNOQW-UHFFFAOYSA-N 0.000 description 1
- VEEFADFWCHSFIU-UHFFFAOYSA-N 3-methylbut-3-enal Chemical compound CC(=C)CC=O VEEFADFWCHSFIU-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 241000134874 Geraniales Species 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- WTEVQBCEXWBHNA-YFHOEESVSA-N citral B Natural products CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000005454 flavour additive Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000001289 litsea cubeba fruit oil Substances 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000002246 oncogenic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing cis/trans-prenyl-3-methyl butadiene ether by using methyl butynol and isopentenol, wherein the cis/trans-prenyl-3-methyl butadiene ether is cis/trans-prenyl-3-methyl butadiene ether which is an important intermediate for synthesizing citral, and the method comprises the following steps: dissolving methyl butynol, isopentenol, a catalyst and an additive in a solvent, heating to ensure that the methyl butynol is isomerized under the action of the catalyst to obtain isopentenal, condensing and eliminating the generated isopentenal and the isopentenol to obtain cis/trans-prenyl-3-methylbutadiene ether, monitoring by gas chromatography in the reaction process, and finishing the reaction if the raw materials disappear. The method has the advantages of mild reaction conditions, simple and convenient operation, high reaction efficiency, high product yield up to 60 percent and good industrial application prospect.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, relates to synthesis of a citral intermediate, and particularly relates to a method for synthesizing cis/trans-prenyl-3-methyl butadiene ether by using methyl butynol and isopentenol.
Background
Citral (Citral), i.e. "3, 7-dimethyl-2, 6-octadienal", of formula C10H16O is an unsaturated chain aldehyde monoterpene containing two double bonds. It usually contains two 2-double bond cis-trans isomers, a mixture of neral and geranial. Citral is an important natural flavoring agent and additive widely used in beverages, foods and cosmetics commonly found in life due to its strong lemon aroma and flavor, and is widely known and favored for its unique, acceptable and lemon-like pleasant odor. Citral is the main component of citrus fruit peel oil. It is mainly present in orange peels. Essential oils containing citral have been shown to have antibacterial, antifungal and antiparasitic properties, making citral a natural preservative (pharm. res. 2015,32, 2548.). It has been proposed to investigate the possible carcinogenic effect of citral, since it has a common carcinogenic effect. In this study, male and female rats and male mice received microencapsulated pure citral (500-4000ppm) in their diet for 14 weeks or 2 years. No data could be established by the investigator to demonstrate the oncogenic activity of citral in rats and mice. With the increasing use amount of citral, citral obtained from natural resources cannot meet the demand of industrial development, and the synthesis method thereof has been receiving attention.
At present, the method for obtaining citral can be divided into two methods, namely separation and extraction from plant essential oil and chemical synthesis preparation. The extraction from the plant essential oil litsea cubeba oil has the defects of low yield, limited resources, high production cost and the like, and is not suitable for large-scale production; the chemical synthesis method mainly comprises an enol and olefine aldehyde condensation rearrangement synthesis method. Wherein, the method for synthesizing citral by BASF company is to condense isobutene and formaldehyde to obtain a 3-methyl-3-buten-1-ol intermediate, the intermediate can be isomerized into isopentenol and can be oxidized into 3-methyl-3-butenal, and then, the two products are condensed and rearranged by a key intermediate cis/trans-prenyl-3-methylbutadienol ether to obtain citral; 2) the citral synthesis method by Rhone-Poulenc of Ronalukang France directly uses isopentenyl aldehyde and isopentenyl alcohol to obtain citral through rearrangement of cis/trans-prenyl-3-methyl butadiene ether as key intermediate. Thus, cis/trans-prenyl-3-methyl-butadiene ether is an important intermediate for synthesizing citral. However, the current process has the disadvantage of high raw material prices, which significantly compromises the cost advantage of the process.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a method for synthesizing cis/trans-prenyl-3-methyl butadiene ether by using methyl butynol and isopentenol, the invention comprehensively utilizes the existing methyl butynol, expands the application range of the methyl butynol and reduces the production cost of the cis/trans-prenyl-3-methyl butadiene ether intermediate.
The invention is realized by the following technical scheme:
a method for synthesizing cis/trans-prenyl-3-methyl butadiene ether by using methyl butynol and isopentenol, comprising the following steps:
dissolving methyl butynol, isopentenol, a catalyst and an additive in a solvent, heating to ensure that the methyl butynol is isomerized under the action of the catalyst to obtain isopropenal, condensing the generated isopropenal and the isopentenol to eliminate the generated isopropenal to obtain cis/trans-prenyl-3-methylbutadiene ether, monitoring by gas chromatography in the reaction process, wherein the methyl butynol serving as a raw material disappears, and the reaction is finished;
the catalyst is copper salt, iron salt, cobalt salt or manganese salt, and the additive is organic acid.
The chemical reaction equation is as follows:
the invention further improves the scheme as follows:
the catalyst is cuprous chloride or cupric chloride or the mixture of the cuprous chloride and the cupric chloride.
Furthermore, the additive is one or more than two of crotonic acid, p-toluenesulfonic acid, hydrochloric acid or trifluoroacetic acid.
Furthermore, the solvent is one or a mixture of more than two of toluene, chlorobenzene, fluorobenzene, xylene, anisole, DMF or DMSO.
Furthermore, the mass ratio of the methylbutinol to the catalyst to the additive is 1000: 10-30: 1-10, and the molar ratio of the methylbutinol to the isopentenol is 1: 1.8-2.2.
Further, the reaction temperature is 120-160 ℃, and the reaction time is 2-16 h.
And further, after the reaction is finished, filtering and separating the catalyst, carrying out reduced pressure rectification on the filtrate, recovering the solvent, and further carrying out rectification to obtain a cis/trans-isoprenyl-3-methyl butadiene ether finished product.
Further, the catalyst obtained by filtering is recycled for at least ten times, and the catalytic activity is not weakened.
Compared with the prior art, the invention has the beneficial effects that:
the invention provides a brand-new synthesis method of a citral intermediate cis/trans-prenyl-3-methyl butadiene ether, which comprehensively utilizes the existing methyl butynol, expands the application range of the methyl butynol and reduces the production cost of the cis/trans-prenyl-3-methyl butadiene ether intermediate.
The method has the advantages of mild reaction conditions, simple and convenient operation, high reaction efficiency, high product yield up to 60 percent and good industrial application prospect.
Detailed Description
Example 1
Adding 420 g of methylbutynol, 850 g of isopentenol, 500 mL of toluene, 5.0 g of cuprous chloride and 4.3 g of crotonic acid serving as an additive into a 1000 mL reaction kettle, then reacting at 120-160 ℃ for about 6-12 hours, filtering to remove the catalyst after GC shows that the reaction is finished, carrying out reduced pressure rectification on the filtrate, recovering 5.0 g of the catalyst and 490 mL of toluene serving as a solvent, and further rectifying to obtain 456 g of cis/trans-prenyl-3-methyl butadiene ether finished product with the content of more than 90%, wherein the yield is 60%. The catalyst obtained by filtering can be recycled.
Example 2
Adding 420 g of methylbutynol, 850 g of isopentenol, 500 mL of toluene, 5.2 g of cuprous chloride and 4.3 g of crotonic acid serving as an additive into a 1000 mL reaction kettle, then reacting at 120-130 ℃ for about 3-8 hours, filtering to remove the catalyst after GC shows that the reaction is finished, carrying out reduced pressure rectification on the filtrate, recovering 6.0 g of the catalyst and 488 mL of toluene serving as a solvent, and further rectifying to obtain 446 g of cis/trans-prenyl-3-methyl butadiene ether finished product with the content of more than 92%, wherein the yield is 59%. The catalyst obtained by filtering can be recycled.
Example 3
Adding 420 g of methylbutynol, 850 g of isopentenol, 500 mL of toluene, 5.4 g of cuprous chloride and 4.3 g of crotonic acid serving as an additive into a 1000 mL reaction kettle, then reacting at 130-140 ℃ for about 4-8 hours, filtering to remove the catalyst after GC shows that the reaction is finished, carrying out reduced pressure rectification on the filtrate, recovering 5.4 g of the catalyst and 485 mL of toluene serving as a solvent, and further rectifying to obtain 456 g of cis/trans-prenyl-3-methyl butadiene ether finished product with the content of more than 95%, wherein the yield is 60%. The catalyst obtained by filtering can be recycled.
Example 4
Adding 420 g of methyl butynol, 850 g of isopentenol, 500 mL of toluene, 5.6 g of cuprous chloride and 4.3 g of crotonic acid serving as an additive into a 1000 mL reaction kettle, reacting at 130-140 ℃ for about 4-8 hours, filtering to remove the catalyst after GC shows that the reaction is finished, carrying out reduced pressure rectification on the filtrate, recovering 5.6 g of the catalyst and 490 mL of toluene serving as a solvent, and further rectifying to obtain 442 g of cis/trans-prenyl-3-methyl butadiene ether finished product with the content of more than 96%, wherein the yield is 58%. The catalyst obtained by filtering can be recycled.
Example 5
Adding 420 g of methylbutynol, 850 g of isopentenol, 500 mL of xylene, 5.2 g of copper chloride and 4.3 g of crotonic acid as an additive into a 1000 mL reaction kettle, then reacting at 140-160 ℃ for about 5-8 hours, filtering to remove the catalyst after GC shows that the reaction is finished, carrying out reduced pressure rectification on the filtrate, recovering 5.2 g of the catalyst and 480 mL of solvent toluene, and further rectifying to obtain 440 g of cis/trans-prenyl-3-methyl butadiene ether finished product with the content of more than 96%, wherein the yield is 58%. The catalyst obtained by filtering can be recycled.
Claims (8)
1. The method for synthesizing cis/trans-prenyl-3-methyl butadiene ether by using methyl butynol and isopentenol is characterized by comprising the following steps:
dissolving methyl butynol, isopentenol, a catalyst and an additive in a solvent, heating to ensure that the methyl butynol is isomerized under the action of the catalyst to obtain isopentenal, condensing and eliminating the generated isopentenal and the isopentenol to obtain cis/trans-prenyl-3-methylbutadiene ether, monitoring by gas chromatography in the reaction process, wherein the raw material methyl butynol disappears, and the reaction is finished;
the catalyst is copper salt, iron salt, cobalt salt or manganese salt, and the additive is organic acid.
2. The method of synthesizing cis/trans-prenyl-3-methylbutadiene ether from methylbutynol and prenol according to claim 1, characterized in that: the catalyst is cuprous chloride or cupric chloride or a mixture of the cuprous chloride and the cupric chloride.
3. The method of synthesizing cis/trans-prenyl-3-methylbutadiene ether from methylbutynol and prenol according to claim 1, characterized in that: the additive is one or more of crotonic acid, p-toluenesulfonic acid, hydrochloric acid or trifluoroacetic acid.
4. The method of synthesizing cis/trans-prenyl-3-methylbutadienyl ether from methylbutynol and prenol according to claim 1, characterized in that: the solvent is one or more than two of toluene, chlorobenzene, fluorobenzene, dimethylbenzene, anisole, DMF or DMSO.
5. The method of synthesizing cis/trans-prenyl-3-methylbutadiene ether from methylbutynol and prenol according to claim 1, characterized in that: the mass ratio of the methylbutinol to the catalyst to the additive is 1000: 10-30: 1-10, and the molar ratio of the methylbutinol to the isopentenol is 1: 1.8-2.2.
6. The method of synthesizing cis/trans-prenyl-3-methylbutadienyl ether from methylbutynol and prenol according to claim 1, characterized in that: the reaction temperature is 120-160 ℃, and the reaction time is 2-16 h.
7. The method of synthesizing cis/trans-prenyl-3-methylbutadiene ether from methylbutynol and prenol according to claim 1, characterized in that: after the reaction is finished, the catalyst is filtered and separated, the filtrate is rectified under reduced pressure, the solvent is recovered, and the cis/trans-prenyl-3-methyl butadiene ether finished product is obtained by further rectification.
8. The method of synthesizing cis/trans-prenyl-3-methylbutadienyl ether from methylbutynol and prenol according to claim 7, wherein: the catalyst obtained by filtering is recycled for at least ten times.
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|---|---|---|---|
| CN202210457180.0A CN114773168A (en) | 2022-04-28 | 2022-04-28 | Method for synthesizing cis/trans-prenyl-3-methyl butadiene ether by using methyl butynol and isopentenol |
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| CN202210457180.0A CN114773168A (en) | 2022-04-28 | 2022-04-28 | Method for synthesizing cis/trans-prenyl-3-methyl butadiene ether by using methyl butynol and isopentenol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101381290A (en) * | 2008-10-30 | 2009-03-11 | 浙江大学 | Continuous gas phase reaction method of isoprene-3-methyl butan-2-alkenyl ether |
| CN101381292A (en) * | 2008-10-30 | 2009-03-11 | 浙江新和成股份有限公司 | Continuous preparation method of 3-methyl-2-propylene aldehyde |
| CN106977383A (en) * | 2017-03-10 | 2017-07-25 | 万华化学集团股份有限公司 | A kind of method for preparing citral |
| CN110028392A (en) * | 2019-04-29 | 2019-07-19 | 山东新和成药业有限公司 | A kind of method of methyl butynol iso-synthesis isoamyl olefine aldehydr |
| CN112574018A (en) * | 2020-11-30 | 2021-03-30 | 万华化学集团股份有限公司 | Low-color-number citral and preparation method thereof |
| CN113956138A (en) * | 2021-11-15 | 2022-01-21 | 江苏宏邦化工科技有限公司 | Method for continuously synthesizing isopropenal through tubular reactor |
-
2022
- 2022-04-28 CN CN202210457180.0A patent/CN114773168A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101381290A (en) * | 2008-10-30 | 2009-03-11 | 浙江大学 | Continuous gas phase reaction method of isoprene-3-methyl butan-2-alkenyl ether |
| CN101381292A (en) * | 2008-10-30 | 2009-03-11 | 浙江新和成股份有限公司 | Continuous preparation method of 3-methyl-2-propylene aldehyde |
| CN106977383A (en) * | 2017-03-10 | 2017-07-25 | 万华化学集团股份有限公司 | A kind of method for preparing citral |
| CN110028392A (en) * | 2019-04-29 | 2019-07-19 | 山东新和成药业有限公司 | A kind of method of methyl butynol iso-synthesis isoamyl olefine aldehydr |
| CN112574018A (en) * | 2020-11-30 | 2021-03-30 | 万华化学集团股份有限公司 | Low-color-number citral and preparation method thereof |
| CN113956138A (en) * | 2021-11-15 | 2022-01-21 | 江苏宏邦化工科技有限公司 | Method for continuously synthesizing isopropenal through tubular reactor |
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